


Do That Again

by Anonymous



Category: Critical Role (Web Series)
Genre: AFAB Caleb Widogast, AMAB Mollymauk Tealeaf, Anal Fingering, Blow Jobs, Genderfluid Mollymauk Tealeaf, Kissing, Light Dom/sub, Mollymauk Tealeaf Lives, Oral Sex, Other, POV Caleb Widogast, Plot What Plot/Porn Without Plot, Sex Toys, Strap-Ons, Tail Sex, Tails, They/Them Pronouns for Mollymauk Tealeaf, Tiefling Biology
Language: English
Status: Completed
Published: 2021-03-11
Updated: 2021-03-14
Packaged: 2021-03-17 23:02:28
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 8,186
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29973630
Author URL: https://archiveofourown.org/
Summary: Tieflings were originally created for a purpose. Corrupted by devils, tieflings were crafted in the image that their infernal overlords found most pleasing. They were made to serve, the price paid for pacts made between their human ancestors with the devils who now owned them. And to ensure they served best, these devils crafted their bodies in ways that have lasting effects to this day.Molly and Caleb get together for the first time and they both discover something interesting about tiefling physiology when Caleb's hand strays too low. Molly absolutely wants to explore this, and they get together again to test the effects of tieflings' built-in submission switch.
Relationships: Mollymauk Tealeaf/Caleb Widogast
Comments: 4
Kudos: 98
Collections: Anonymous





	1. Chapter 1

**Author's Note:**

> Both Caleb and Molly refer to their genitals as their "cocks" in this fic. Most of the rest is up to your imagination~*~*
> 
> Caleb doesn't get penetrated at all in this fic, if that bothers you. There is mutual oral in chapter 1 and Caleb will top in chapter 2.

The first time that Mollymauk approached him was their first night back in Zadash. Caleb had returned to Chastity’s Nook in search of something to distract himself from the memories of the last month, and had found just the thing. For a book from a smut shop it was a thick tome, with as much plot and intrigue as there was sex. He was savouring it as he lounged near the hearth in the common room at the Pillow Trove, relaxing in a wingback chair.

Nearly losing Mollymauk had taken a toll on them, and the moment that they’d arrived at the hotel Molly had paid for a private room and disappeared upstairs, presumably to order a companion or two. Caleb couldn’t blame them for wanting another night of comfort: it was probably a welcome distraction from the memory of waking up on the side of the road with a mouthful of blood and all their friends looking down on them. Caleb wished he could forget the image from his own perspective, of Molly splattered with blood, limp on the ground as Lorenzo and his crew rode off. They had been lucky that the Iron Shepherds had been in a hurry, otherwise they may have given chase when the rest of the Nein scattered into the woods.

But Caleb wasn’t comfortable with the same sorts of distractions as Mollymauk. He feared strangers seeing him without the armor of the façade he wore, dressing himself in mundanity that caused most eyes to skim right over him. Being seen was something that made his skin crawl. So he curled up with his book and forgot about the world for a while, pausing from time to time to scan the room around him. Just as the first tryst in his novel was about to begin he stretched and looked up, jumping when he discovered that Molly was sitting in a chair next to him. The tiefling was staring into the fire in deep introspection, eyes unblinking and glazed over. The spade of their tail flicked gently, like Frumpkin’s did when he was restless.

“Ah, _hallo,_ Mollymauk. I thought you would be enjoying your private room.”

Molly’s eyes unglazed a little, but they continued to stare into the flames. “Just wasn’t in the mood. Haven’t been too fond on letting total strangers get near me, you know, since…” They sighed. “But once I was up there, I realized I didn’t want to be alone, either.”

Understanding how they felt, Caleb nodded. Strangers in general made him uncomfortable, but the idea of letting one near his body? A shiver ran through him.

Breaking their gaze from the hearth, Molly looked at Caleb. “So what are you reading? Must be captivating. You’ve been there for nearly an hour without moving since I came down.” A tiny smirk quirked at the corner of their mouth, dimpling their cheek.

“Just some light reading to take my mind off things,” Caleb said hastily, and closed the book without a bookmark. He knew he would remember the page, and with any luck if Molly were to open the book to a random page, they would only get an eyeful of plot.

“Mmhmm…” Molly hummed, their eyes all-too knowing. “Well, it’s late, and I was about to go to bed. Looks like you were about to do the same.” Their voice was teasing, and Caleb flushed. It was true, his intention had been to go upstairs and enjoy the next scene in privacy. The buildup had been long but satisfying, and Caleb ached to go relieve the tension that had wound over the last three chapters of flirtation between the characters. If Molly had been watching him for an hour as they said, they’d probably noticed his breathing intensifying during that time, and the flush that had crept over his fair skin. He averted his gaze guiltily, looking into the fire.

“You’re welcome to come read in my room, you know. I’m sure it’s more comfortable than these straight-back chairs.”

The words rang in the air for a moment as Caleb processed the offer. He looked back at Mollymauk, who was waiting and watching him with trepidation. Opening his mouth to speak, only a little strangled sound came out. Molly’s eyebrows pinched.

Caleb suddenly felt very hot where he sat. He was hyperaware of his body: heart beating a rapid patter in his ears, trousers tight and a little damp, breaths shallow and rapid. He wondered what he looked like in that moment, frozen like a deer in the light of a bullet lantern. Were his pupils blown-out? Had the flush spread to his chest?

He stood from his chair like a bolt and clutched the book to his chest with both hands, suddenly worried that he wouldn’t be able to keep his breathing under control if he stayed under Molly’s gaze. Despite their lack of pupil, he could feel Molly’s hungry gaze sweep over his body.

It was a lot to process all at once. They had of course been flirting with him for more than a month, but Caleb had dismissed most of that banter as more of Mollymauk’s bravado. They flirted with plenty of people when it suited them, and Caleb knew that he was nowhere near as appealing as those other people. But the way Mollymauk was looking at him now spoke of a real attraction.

Caleb couldn’t deny that he was attracted to Mollymauk himself. They were beautiful, handsome, confident, jovial. Their personality burned brightly in a way that Caleb could only dream of. That he had seen them naked mere hours ago at the baths was not helping his situation. He could feel his blood rushing southward as he deliberated, aware of just how long the silence had gone on. Scrunching his eyes closed and willing himself to make a decision, he nodded.

Over the gentle cracking of the fire, he heard Molly stand. He was so grateful that the room was otherwise empty when their lips met his in a soft kiss, as a little moan escaped his throat unbidden. He let Molly lead him along by the wrist, up the stairs to the first room on the left. They opened the door and stepped inside, leaving Caleb in the hall, and looked at him questioningly.

With shaky legs, Caleb entered and closed the door behind him, placing his book on the dresser to his side. He began to unfasten the straps of his book harness, mentally cursing himself for not having had taken it off before sitting down to read. The straps had likely left lines on his back.

Molly sauntered up behind him as the holster slipped free and ran their hands along his shoulders. When the books were safely on the dresser, Caleb turned to face them and was rewarded with a gentle push backward. His lower back hit the drawers with a clunk and then Molly was in his space, leaning up to kiss him again. They brushed against Caleb’s thigh and he could feel their interest already, which sent a jolt of arousal southward. Moaning into the kiss as Molly’s fingers threaded in his hair, he reached down and began to rub them through their leggings.

The response was immediate. Molly’s fingernails dug into his scalp and they leaned into the contact, so Caleb undid their belt and let it fall to the floor. He fumbled at the waist of their leggings, but the damned things were too tight to get his hand inside and Molly was laughing into his mouth. He felt for a button, a buckle, a tie, anything, but found nothing. He broke from the kiss and looked down, puzzled by this unexpected barrier.

Still laughing, Molly guided his hand to the small of their back, where Caleb found a simple closing with two buttons over their tail. He opened them and pulled Molly’s shirt free, feeling the knobbly bumps of their spine as it curved gracefully out into that slender tail that Caleb had thought so much about. They shivered a bit under his touch and grabbed the crotch of his own trousers, rubbing their hand over him.

Caleb froze at the touch, not having expected it so soon. It was fine, he assured himself. Molly was diverse in the gender department themself, and he knew them to not care about a partner’s genitals, but the memories of other rejections still came to mind. He dropped to his knees, sliding out of their reach, and started peeling their leggings down their legs. Shoving the memories away, he focused on Mollymauk.

They were every bit as beautiful as he remembered, even more so now that they were hard. Their cock sprang free as he pulled the leggings down and it bobbed in front of his face, tapered and with fine ridges along the bottom. Caleb wondered what it would feel like on his tongue. He pulled the garment free of their legs and wasted no time in getting to work, pushing their cock into his mouth and letting his hands roam over their hips.

Molly was responsive and gentle as he explored, licking their shaft and sucking on the head with his lips. He looked up to find them looking down at him and he blushed, dropping his gaze and closing his eyes to focus on the sensations and sounds. Under the pads of his fingers he felt their spine again, tracing lower until his hand was on their tail. It earned a shiver and a moan, so he stroked down the appendage as best he could with it thrashing about.

Then he moved his hands to their ass, kneading the firm muscle there and tracing the curve of their cheeks. He traced down the back of one thigh as he tried to relax his throat around their cock, allowing the other hand to roam back to their tail.

Tracing his fingers along the underside of their tail had an immediate and strong reaction from Molly. They immediately straightened, back curving in an arc and pushing their cock forward into Caleb’s throat. He gagged on it but was able to pull back, and looked up at them to see if the reaction had been a good or bad one.

The look on their face was one of shock, but in the lamplight Caleb could see the light reflecting in their hidden pupils. Their pupils were wide — wider than Caleb had ever seen, and when the shock wore off their face melted into one of pure lust. It seemed Caleb had found a sensitive spot.

He ran his fingers along the underside of their tail again, this time with a bit more pressure lest the last time had tickled. Molly jerked again and their tail ceased its wandering, coming up high to curve over them. They moaned and then panted at the touch, so Caleb went back to their cock and began to suck again eagerly.

With the combined attention his mouth and hands were giving, Molly came in less than a minute, moaning deeply all the while. Their chest actually vibrated with deeper tremors when they came, a sound that he’d heard at times when they spoke Infernal, and the vibrations continued even after their voice had quieted.

Knees groaning at the rough treatment, Caleb moved out from under them and stood. Molly was barely standing, braced against the dresser with both hands and bent over slightly. They were breathing hard, harder than Caleb had ever seen someone do during sex, more akin to the aftermath of a sprint, and his brow wrinkled in worry.

“Mollymauk are you alright? Did I—” Molly raised a finger, taking a moment to catch their breath before responding.

“That was— you— I—” They drew a final deep breath and straightened. “I don’t know what you did, but it felt like you literally sucked my brains out.”

“Oh.” Caleb didn’t know what to say to that. He was, in his own opinion, very rusty at this, and had absolutely no experience with a tiefling partner. Whatever he had done he had stumbled onto by accident, but judging by Molly’s reaction it was entirely new to them as well. “Has nobody ever touched you there before?”

“Gods, no. I may be a big talker, but our last time at the Pillow Trove was the most serious sexual encounter I’ve ever had before this, and those two weren’t exactly experienced with tieflings. I got a massage and a handjob and a lot of attention.” They slipped their shirt off, now damp with sweat, and wiped their brow with it before tossing it aside. “And before that I was with the carnival. I’ve had a few quickies with people, but those are… quick.” They snorted and moved to the bed, pulling back the covers and sitting with one leg folded under them. “Come here, then. I want to return the favour.”

A bit shyly, Caleb crossed the room to sit beside them. They pulled his shirt out of his trousers, which were much looser on his thin frame than their leggings had been on their own, and slipped a hand underneath to stroke the neat line of hair that trailed down his belly.

“Anywhere off-limits?”

Caleb hesitated, trying to think of a way to explain what he wanted without using words he found distasteful. “Ah, nowhere… inside, please.” Molly nodded and let their hand roam higher, combing through his chest hair and rucking up his shirt. Caleb pulled it over his head and put himself on display, only folding inwards a little when Molly’s eyes roamed over him. They leaned in to press a kiss over his heart.

“You’re gorgeous,” they breathed over his skin before pressing another kiss there. “Absolutely gorgeous.” Caleb was about to protest when they kissed his nipple, sending shockwaves through his body and knocking the thought from his mind.

Deft hands began to untie his trousers and then his smallclothes, pulling them from his hips as Caleb squirmed under Molly’s tongue. Hands itching to grab something, anything, Caleb reached around Molly and swept his fingers down their spine, reaching for their tail. A hand snapped up to grab his wrist as his fingers closed around the appendage and Molly straightened, holding his hand aloft between them.

“Darling, if you keep that up I am going to be begging for you to fuck me, and I’m not sure if you’re up for that yet.”

“Oh,” Caleb said again, feeling dumb. “Yet?”

Molly practically purred. “Well _I_ certainly hope there’ll be a next time. But first, why don’t you lay back and let me make you feel good?”

Caleb did lay back on his arms, allowing Molly to pull away his now very damp clothes and expose him to the air. He curled his knees up reflexively, suddenly feeling very exposed as Molly drank in the sight of him. They frowned and sat on the bed again, putting a hand on his.

“You know you don’t have to do any of this, right?”

“No, I mean _ja._ I mean... Mollymauk, I want to. I am just… It has been a long time, and I am…” He waved a hand in front of his body, vaguely gesturing at the tangle of red curls between his legs and making a pained face.

Molly just looked confused. “And you’re gorgeous, yes. What’s the problem?”

Unable to describe how he was feeling, Caleb sighed and relaxed his legs. “It is nothing. Please forget I said anything.”

“So can I…?” Their hand hovered above his knee.

“ _Ja,”_ Caleb affirmed, then fell back as Molly started caressing one of his thighs.

“With pleasure,” they purred, and knelt down to lick at his cock.

It was a bit difficult at first to find a way to accommodate Molly’s horns between his legs, but once they found a position Molly gave head like a champion. Despite their professed lack of experience, they had enthusiasm in droves and quickly learned how to pull Caleb undone with their mouth. True to their promise, they didn’t delve anywhere lower than Caleb’s cock. He was grateful for that, and even more grateful when they took to sucking him like he was much longer than he was in reality, bobbing their head up and down with their lips around his shaft. He moaned at that and stuffed a hand into his mouth to muffle the sound.

It wasn’t long before Caleb was coming with a shudder with Molly’s mouth on his cock and one hand lightly pulling his chest hair. He bit into the meat of his hand as he rode through the waves of pleasure, trying and failing to stifle the groan in his throat.

When his hips stilled, Molly lifted off his cock with a gentle _pop_ that made Caleb twitch from overstimulation. Suddenly overwhelmed, he slung a hand over his eyes began to laugh.

“That good, huh?” Molly asked, reclining next to him. Caleb shook his head and laughed silently for a moment more.

“ _Nein,_ no, I just cannot believe this is real.”

“You’d better believe it,” they purred, scooting in to cuddle against his side. “And like I said, I want it to happen again. I don’t know what you found earlier, but I’ll be damned if I pretend that didn’t happen rather than explore it to its fullest.”

Caleb unshielded his eyes and turned his head to look at them. “What did it feel like?”

Molly’s mouth quirked as they thought for a moment. “It felt like a lot of things all at once. It was like lightning up my back, and I wanted to curl my tail up and stick my arse out and be fucked more than anything. But I also wanted to lay down and close my eyes and not think. Everything kind of went… it was like I was in a tunnel. All I could think about was how good it felt and how much I wanted you.” Their tail snaked around Caleb’s thigh. “And if you’re willing, I want to try that again. See where it goes.”

“You want me to fuck you?”

“Sure. However you want to. Hands, objects, whatever fancy magic tricks you’ve got up your sleeve. You’ll find I’m very flexible.”

Caleb wheezed out a cough at that idea. “I do not know any tricks for that, I am afraid.”

“Pity. But I’m sure we’ll think of something. So what do you say? Are you up for more fun and a little exploration?”

An ache filled Caleb’s heart. He did want to, more than anything, but part of him couldn’t accept that Molly would want to fuck him, of all people.

“Why me? I am sure you can find many people willing who are much more handsome than me, and with larger cocks.”

“Oh, none of that.” They swatted at him, but it was gentle. “I find _you_ handsome. I like _your_ cock. And it’s _you_ that I feel safe with, and that’s the most important part.”

Caleb blushed and he hid his face by turning away, trying to get a handle on his shyness. He’d just had sex with the tiefling and they were still laying together naked, why were compliments flustering him so?

“I… would be willing to help, Mollymauk. I enjoyed this very much.”

They beamed, and the spade of their tail tapped happily.

“Let me know when you want to. I’m always willing to fork out the gold for a private room when I’ve got a good reason. And this is a damned good reason.” They kissed his shoulder and curled closer, yawning. “Now if you’ll excuse me, I’m going to sleep, because some handsome wizard sucked all the energy right out of me.”

Resigned to his fate pinned under Molly’s arm and tail, Caleb waved a hand to extinguish the lamps and closed his eyes. Despite everything this still felt like a dream, and he couldn’t help but wonder which bed he’d find in himself come morning.

That didn’t stop him from thinking about the next time, though, and as he drifted off to sleep he wondered if the proprietor of Chastity’s Nook could recommend him a shop with a slightly different selection of products.


	2. Chapter 2

**Notes for the Chapter:**

> Hi so this was supposed to be a bit more dom-y but I only know how to write soft things so... enjoy?

Caleb looked over his shoulder before ducking into the store that Iva had recommended to him. He was in disguise, but you could never be too careful when you had nosy friends.

The shot itself was nondescript, featuring a window display of used books and velvet curtains that blocked view into the shop itself. A bell chimed as Caleb entered, heralding his arrival when he very much wanted to remain unnoticed. He cringed as the shopkeeper waved to him, and immediately ducked around a display that featured a variety of collars and harnesses.

He knew what he was looking for: he’d read enough smut to know that such things existed. It wasn’t difficult to find in this small shop; an entire row of the displays were filled with cocks of a variety of shapes and sizes. He honed in on a group of them that matched his skin tone, hoping that it would make it feel more like an extension of his body and less like he had an object strapped to him.

The prices on some of the items left his head spinning, though upon closer inspection their tags promised an enchantment that would allow the wearer to feel the item like a part of their body. It was a tempting promise, but one Caleb simply didn’t have the money for. He filed the detail away for later, then caught himself. Why was he thinking about ‘later’ as if this thing with Mollymauk would continue? Surely they would move on before he could afford such a thing. Scoffing at himself, he returned his attention to the items within his price range.

Soon he had it narrowed down to two choices. They were very similar, but one was a little thinner than Molly, and the other slightly more thick. Caleb bent down to scrutinize the items behind the glass, wondering if it would be better to start off with something smaller or not.

“Can I help you with anything?” Caleb jumped at the unexpected voice behind him, straightening lightning fast and turning around as if he’d been caught doing something wrong. A flush rushed to his face, but the shopkeeper only looked at him pleasantly.

“I, ah, must profess that I have no experience in this… area,” he admitted, wringing his hands. The shopkeeper nodded knowingly, then pulled out a small key.

“Why don’t you tell me about your intended use and I’ll bring these out for you to take a closer look at?”

Caleb couldn’t help but stammer, flustered at the unwanted attention, but he supposed he could use the help. Staring at his toes, he told her what he needed in a mumble.

“Hmm,” she hummed, removing a few of the peony petal-coloured cocks from the display case and putting them on its top. “How about your partner? I can help you choose a size if I know more.”

Five minutes of humiliation later, Caleb was at the counter with a thick pink cock in one hand and a soft harness in the other. The shopkeeper gave him an appraising look as he counted out his coins, then pulled something from under the counter. It looked remarkably like a scroll tube, if a bit large, and even had a few fake runes inscribed on it. “You look like the type,” she explained as she packed his items neatly away into it. “Keeps everything clean and away from prying eyes.” She put the tube into a nondescript paper bag, then, seeming to make a split-second decision, she grabbed a small vial of oil from a shelf and added it as well.

“Spell components,” she said with a wink, and slid the bag forward. “Not that you’ll likely need it, given what you’re doing. But just in case.” Caleb thanked her and grabbed it, clutching it to his chest as if someone could know what was inside if he so much as lowered an arm. Darting out into the street, he made his way back to the inn.

They had moved to a less expensive inn in the days since Caleb and Molly’s night together at the Pillow Trove, and Caleb’s heart beat rapidly the whole way back from the Tri-Spires. He stashed his purchase at the bottom of his pack and went looking for Molly. It didn’t take long to find them; the tiefling stood out in a crowd and hadn’t wandered far. Caleb approached them as they were trying on an ear cuff at a small jewelry stall and waited for them to finish.

“Oh, hello dear,” they said, fiddling with the earring. “Is it that time already? You’ve got that look on your face.” When Caleb could only stammer in response, their face split into a wicked grin and they slapped a gold into the jeweler’s hand. “Don’t you worry. I’ll take care of everything.”

  
  


It wasn’t long before Caleb was being pulled along by the hand in the twilit streets of Zadash to a building not a few blocks away. “Found the perfect place,” Molly said. “Sound-proof rooms. May or may not be an illegal temple of the Moonweaver.” Only once they were inside their rented room with the door closed behind them did Caleb really snap into the present, the full weight of what was about to happen settling over him heavily.

Molly wiggled out of their ridiculous boots and sat on the edge of the bed, legs kicking in the air with excitement. Their leggings were new and Caleb took a moment to admire them, the garment so uniquely Mollymauk that he wondered where they could have possibly found such an item. The starry fabric was as tight as ever, held in place with stirrups under the arch of each foot so that they were smooth the whole way down their legs.

“Before we start, I just want to set a few limits. I figure I might not be able to talk once we start, and even though you don’t seem like the kind of fellow who’ll surprise me with anything, I’d rather that you know what not to try before we start.”

Caleb swallowed dryly and took a seat opposite them in the room’s chair. “Alright.”

Molly raised a hand with one finger extended. “First off, no piss or shit or blood.” They raised two more fingers as they spoke, counting off their restrictions. “Don’t gag me with anything unless I can answer you to ask for it. Same with restraining me. If I feel like I’m buried I’ll probably try to claw my way out and it won’t be pretty for you.” They waggled their fingers in a mock threat, showing off the pointed tips of their painted nails. “And the most important thing: at any moment if I say ‘empty,’ you have to stop right away and get Yasha, because it means I’m well and truly fucked in the head.”

A surge of emotion rushed through Caleb as they opened up their vulnerabilities to him. He knew that as much as they wanted to enjoy this, they were trusting him with their safety and comfort. He reached out to take their hand, stroking their knuckles comfortingly with their thumb.

“I will remember,” he promised, and brought their hand up to kiss it.

Then they were moving on to the main event, as Molly pulled on their conjoined hands to lift Caleb off the chair and into their reach. Shirts were quickly shed so that Molly could bury their face in Caleb’s soft chest hair, tickling at his skin with the light brushes of their nose and lips.

Caleb’s trousers came off first, only because they were so loose and easy for a devious partner like Molly to slide down during a change in positioning. This time Caleb found that he didn’t care nearly as much about his nakedness, feeling very safe with Molly. That their eyes were closed as they kissed him passionately also helped. As they felt up his skinny backside, he fiddled with the clasp above their tail and started to peel down their impossibly tight leggings.

“Oh, thank the Moonweaver,” Molly moaned as their cock was finally freed from its cotton prison.

“You should have asked, _Schatz,”_ Caleb laughed as he eased the garment down their legs.

“I was preoccupied with a handful of hot wizard,” they protested, pulling one leg in opposition to Caleb’s grip on their pants. Their foot popped free and they were in the nude at last. Folding their clothing before setting it aside, Caleb planted a soft kiss to the top of the lavender foot before him.

“I thought this night was supposed to be about you?”

“And I wanted to squeeze your lovely little arse. But if you want to touch mine, you can just say so.” Flipping onto their stomach, they waggled an eyebrow and their ass in the air. Caleb climbed back up to them and began to softly work his way down their spine. There was still a bruise on their back from an earlier job, but it was fading to a dull green. He avoided it nonetheless. When his kisses reached the small of their back, Molly gasped and their tail twitched in anticipation.

Caleb chuckled and stroked one ass cheek softly. “Something you want, _Liebling?”_

Molly lifted their tail, showing off the underside as well as the cleft of their ass. “You know damned well. I bet you’ve been thinking about it nearly as much as I have. Do the thing aga- _ain-nnn.”_ Their voice turned into a moan as Caleb’s fingers stroked the underside of their tail, experimentally starting from the base and running down its length to see which parts got the most response.

Light touches farther from their body seemed to cause them to arc their tail over them for better access, while firmer touches at the very base made them whine and stick their backside out for more pressure. Soon Molly was propped up on their knees, panting as Caleb gently massaged the base of their tail.

They raised a hand and waved it to catch his attention, so Caleb stopped his touches and let them catch their breath. It took some while for them to regain their composure: longer than the last time, and when they did speak their voice was shakier.

“You—” _pant_ “—teasing bastard.” They took a deep breath and looked back at Caleb with their eyebrows furrowed. “What do I have to do to get you to fuck me?”

With Molly like putty in his hands, Caleb couldn’t help but feel a little insolent. He ran a finger under their tail again, about a foot from their body, pulling a whine from their throat as the appendage leapt up to show off their backside.

“You could ask nicely.”

Molly’s face pushed down into a pillow as they gave a small scream of frustration before arcing their back up. “Caleb Widogast, if you don’t touch my arse right now—” The rest of the threat died in their throat as Caleb gave their ass cheek a pinch, pulling a yelp from them.

“That was not a question, _Schatz.”_

“Please, Caleb! Will you _please_ fuck me?” Frustration tinged their voice.

“Okay. But first you will have to wait a moment as I prepare a few things.”

Molly groaned and dropped their face into their arms as Caleb stood, so he stopped to stroke their hair before going to his bag. He retrieved the false scroll tube that contained his purchases, returning to the bed to set them out. Molly rolled over to watch him step into the harness and attach the light pink cock that he’d purchased, adjusting until everything fit snugly. Their hand roamed down to their own cock as they watched, palming it gently with a hungry look in their eye.

“Get comfortable, _Liebchen,”_ Caleb said as he climbed up on the bed and sat with his legs folded beneath him. The straps of the harness pulled taught but did not pinch, and the cock between his legs bobbed as he settled. Molly’s eyes followed it, and they licked their lips absently.

It took a moment for his words to register before Molly was saying “right, sorry,” and arranging themself on their knees and elbows with their ass in the air. With the little bottle of oil in one hand, Caleb began to caress their cheeks with the other. Molly immediately began to hum and shudder at the light touches, head slowly dipping toward the mattress.

As before, Caleb took his time cataloging their reactions. Swirling a finger around their rim caused them to inhale sharply and curse, and the muscle fluttered with anticipation. It was curiously slick, not unlike how Caleb probably was between his own legs right now, and he gave another experimental swirl.

More touching at the base of Molly’s tail both brought more slick and caused them to bow down into the feather bed, chest vibrating with a faint purr. Eased by the slick he had caused, Caleb slowly slid a finger inside them, smiling when Molly gave a wordless moan. It was an easy thing, their ass parting for him with little resistance as he gently pushed inside. He massaged a bit as they opened further, then slipped another finger inside. All the while, he kept a gentle pressure at the base of their tail, which was lifted over them in an arc and quivering slightly.

Removing his hand from their tail for a moment, Caleb stroked Molly’s hair. “You are doing so well,” he praised, scratching their scalp gently. The only response he got was a soft whine. “Do you want more?”

“Hrrrm,” Molly whined loudly, shaking their head yes and causing their curls to bounce. Their hair was getting long, now trailing to their shoulders in the back and hanging in their eyes nearly constantly. Caleb gave them one final ruffle before he returned his attention to their ass, enjoying the silky smooth texture of their hair.

Looking at the thickness of the cock he’d purchased, Caleb decided that one more finger would be a prudent precaution. Even that slid in easily, aided by Molly’s natural lubrication, and Caleb sought out Molly’s prostate as he pumped his fingers in and out of them. Molly was quick to alert him when he found it, groaning into the pillow and intensifying their purring.

The whine that Molly gave when he finally removed his fingers was positively heartbreaking, and they looked at him over their shoulder with a face that practically pleaded. Caleb patted their back as he repositioned, kneeling behind them. Molly pushed back against him as he did, and his cock slid under their body to slide alongside their own.

“If you want this, you will need to get lower,” Caleb chuckled, pulling his cock back. Molly huffed and pulled their knees apart, sliding down until Caleb had a chance of actually being able to slide inside. “Good Molly.” Molly purred louder at that, rubbing up against Caleb’s hips and using their tail to stroke his belly. It tickled, so Caleb put a firm hand on their back and leaned back a bit. “I would like to hear your consent please, Molly.” They whined and leaned back again, but Caleb held them firm and tutted. “Can you use your words, _bitte?”_

There was an answering huff and a growl, then Molly strained and just barely managed to eke out a “please,” more of a whine with consonants than a word. But it was obviously difficult for them in this state, and Caleb was happy that they had tried. He paused to kiss their back before checking that their hole was lubricated enough, remembering that he had oil on hand if needed. But they were more than ready, ass glistening with slick all down the crease.

“Here we go, _Schatz,”_ Caleb warned as he pushed the head of his cock inside. It was thick, thicker than he would have thought to purchase, but the store owner had insisted that for a tiefling it would be fine. He could see now what she had meant, with Molly stretched open so easily and begging for more in their wordless way. Caleb had to hold them firm as he slowly pushed inside, otherwise they would have pushed back all at once and potentially hurt themself. They groaned as he inched inside, stopping only when he was fully seated inside them. Now filled entirely, they paused for a moment to adjust to the stretch, panting.

When Caleb began to move, he did so slowly. Gently rocking his hips, he pulled out and then slid back in, watching Molly’s reactions for any sign of discomfort. Luckily there were none, just blissful sounds in their throat as his cock glided in and out of them smoothly.

He picked up the pace a little, using more force when pushing inside. Molly gave a hum of appreciation and reached back, taking one of Caleb’s hands from their hip and guiding it to their tail. Caleb got the message and began to rub under it with his thumb, eliciting a moan from Molly immediately. The image of Molly like this, debauched and devoid of words, set Caleb grinning. He pushed harder and watched as they continued to fall apart.

Eventually Molly was trilling, a breathy, voiceless sound that sounded like some Infernal inflection that couldn’t possibly be described by the Common alphabet. It built as the shaking in their body did, ebbing and flowing with their breaths. They ground back against Caleb and whined, seeking something more.

Caleb realized that he was probably missing Molly’s prostate in this position, given that they were of a height. But the tiefling was all legs and even with their knees knocked apart, Caleb was probably just barely grazing that spot, leaving them frustrated. That simply wouldn’t do, so Caleb withdrew to reposition.

Molly whined as his cock popped free and they leaned back to chase Caleb, but Caleb placed a hand on the small of their back and pushed them down. Pliant as Molly was in this state, they flopped forward onto the bed with a huff, pulling their legs together to lay more comfortably. Caleb stroked the underside of their tail with a finger, a light touch that was more of a tease than anything, and Molly’s tail lifted above them in an arc as they shivered.

“Plea-ease,” Molly choked out between tremors, fingers gripping the sheets tightly. They lifted their hips in the air as if to rise, and Caleb pushed them back down and straddled their thighs. Molly made such a pretty picture in this state, tail curved artfully to expose the cleft of their ass. And what a pretty ass it was, wet with slick and wriggling as Molly struggled to endure the lack of touching. Caleb caressed a cheek and leaned forward, framing Molly’s body with his own and leaning in to whisper in their ear.

“Don’t worry, _Liebling._ I just wanted to make sure this is as good as possible for you.”

He was rewarded with another shiver and a flick of Molly’s ear against his lips, the point twitching expressively. Brushing his lips against the soft ear tip, he took one of Molly’s hands in his and guided it down to their waist, encouraging them to slip the hand between their body and the bed to palm their own cock. Molly did so and groaned, grinding into the mattress under Caleb.

“Shut up and fuck me already,” Molly hissed, turning their head to gently push at Caleb with the curve of their horn. The rough keratin rasped against Caleb’s beard and he chuckled, and propped himself up over Molly’s body once more. They gnashed their teeth and flashed their fangs at him, growling. Their tail was lashing now, but one touch at its base and it was rigid again, lifted to provide access to their backside. The aggressive sounds stopped as they melted again at the touch, and Caleb chuckled.

“For one so mouthy you are very easily put in your place,” he mused, and rubbed his cock between their cheeks. Molly only whined in response and wiggled weakly under his thighs. “But since you asked me, and you have been so good, I will do as you ask.” With gravity to aid him, Caleb lined up the tip of his cock with their entrance and slowly pushed inside. “You will tell me if this angle is good for you, _ja?”_

The answering moan and nod of Molly’s head told him all he needed to know. Rocking in and out of them as he rubbed the underside of their tail, all the fight bled out of Molly. Caleb fucked them firmly but not fast, focusing on hitting their prostate and watching their pleasure build. The purring returned, a vibration that shook their entire body, and Molly’s tail curled loosely around Caleb’s waist. It felt oddly intimate — more so even than the sex — and Caleb brought the spaded tip up to his mouth for a kiss.

A sigh escaped from Molly below him, an airy thing that turned into a trill again as the purring continued. They canted their hips up and moaned at the angle change, using the added space between their body and the bed to rub at their cock more quickly. Their hand was shaking, as was much of their body, and Caleb wrapped a hand under them to take over.

“Let me, _Schatz._ You just relax.”

Molly’s contented sigh as they let their hand fall away told Caleb so much about how relaxed they were. He took up stroking their cock at a rhythm in time with his thrusts, building speed slowly as Molly started moaning more and tensing their once-pliant muscles. Watching their back flex with all the intricate ink on it was beautiful: a true work of art.

When the tremors started, Caleb knew that they were close. Molly’s breathing reduced to a pant, and they threw their head back and began to push back to meet Caleb’s thrusts. He snapped his hips and gripped their cock more firmly, and Molly began to growl deep in their throat. The growl turned into a moan as it raised in pitch, and then Molly spat some Infernal word as they came, whole body shaking as they collapsed onto the bed. Caleb slowly pulled out and Molly mewled but did not move, and Caleb crawled off the bed to remove his harness.

Stepping over to the vanity, he poured some water on a washcloth and washed between his legs. He was embarrassingly wet, with slick halfway down his thighs despite not having been touched any more than the slight pressure that fucking Molly had provided. Now clean and with the water cooling his skin, he turned back to the bed, ready to clean Molly up and cuddle as they came down from their high.

When his knees hit the bed, Molly roused. Looking up at him, they smiled and lifted their head, making grabby hands and reaching for his hips.

“ _Hallo,”_ Caleb laughed as they kissed his navel and wrapped their arms around him. They wiggled lower, poking through his body hair with their nose as they moved downward. It tickled. Caleb laughed and jerked in their arms, trying to escape the teasing touch. “You should rest,” he protested, lifting Molly gently by the chin as their lips grazed into his pubic hair. They pouted and _harumfed_ at him, pushing against his hand to nuzzle at his navel again.

“Wanna,” they grunted, mind probably still foggy from their orgasm. But their intention was clear, and Caleb’s heart skipped a beat at their attention, his previously softening cock flooding with interest. He released their chin and moved to stroke their hair as they worked lower again, and he gasped when their lips finally grazed his cock.

They teased him with nothing but gentle licks and kisses at first, coaxing him back to hardness as his cock swelled back to its full length. When they finally took him in their mouth Caleb groaned, realizing just how wound up he had been. They wasted no time in sucking him as they had before, working their mouth along his length like he had a cock as long as the one he’d fucked them with earlier.

Hands grazed lightly down the backs of Caleb’s thighs with the lightest touch of sharp nails, sending shivers down his spine and making him buck into their mouth. Molly grinned and licked him once more, then rolled onto their back on the center of the bed and patted their chest.

It took a moment for Caleb to understand what Molly wanted, and he straddled their chest tentatively, not wanting to crush them. But when Molly pulled him down and sucked his cock back into their mouth, all doubt fled his mind. Grabbing the headboard for support, Caleb ground down into their mouth and moaned.

Soon Caleb’s legs were shaking and his orgasm was washing through him like a wave, world reduced to the sensations around his cock and the eight pinpoints of pressure of Molly’s nails on his ass cheeks, holding him steady as he lost control. Molly hummed contentedly as he rode through his orgasm and collapsed to the side, curling around him and pressing their wet chin against his back.

“That was amazing,” they mumbled against him some time later. “I’ll get a room with you any time, Mister Caleb. Just say the word.”

Never had Caleb been so grateful that someone could not see his face as in that moment. A rush of guilt and sadness washed through him unbidden, mind immediately racing to justify why he did not deserve this praise. There was no way that someone as beautiful as Mollymauk would want him, of course.

Apparently his lack of response alerted Molly that something was wrong, because they sat up behind him and tried to turn him with a gentle push of their hand.

“You enjoyed this, right, love?” they asked, worry evident in their voice. Caleb’s guilt intensified.

“ _Ja,_ I did,” he croaked, fighting against the emotion that blocked his throat.

“Then what’s wrong?”

Caleb pressed his eyes shut and took a deep breath. He didn’t have the words to convey everything he was feeling right now, and he would have sunk into the mattress never to be seen again if he could’ve. But he couldn’t, so he formulated a simple explanation.

“I… I do not deserve this.”

Molly snorted. “Oh _ja_ you do,” they retorted, their mockery of his accent a crime against Zemnians everywhere. Caleb couldn’t help but crack a half-smile, half grimace. “Everyone deserves to feel good sometimes, self-deprecating wizards included. You’re much too hard on yourself.”

“I am—” Caleb began, but was cut off when Molly leaned around to nip at his belly with their teeth. His ticklish body betrayed him and his words disappeared as he yelped from the contact.

“...very ticklish, apparently,” Molly laughed. “But you’re also charming, gorgeous, selfless, and damned attractive when those fingers of yours are weaving magic. And I’m setting a new rule: no insults in bed, unless you’re calling me a nice little slut or something. But that’s not an insult, really. But regardless—” Molly poked a finger to Caleb’s sternum accusingly “—you’re lovely and I won’t let you talk yourself down. Now, do you want to stay here tonight, or sneak back to the inn and pretend we were never gone?”

Caleb considered. He wasn’t sure he could handle the teasing that would surely come his way once the group knew about him and Mollymauk, but he also felt exhausted and the prospect of sleeping alone was not a fun one. In lieu of an answer he rolled over and curled up against Molly, resting his head over their heart. Fingers carded through his hair soothingly.

“Alright, love,” Molly purred, and when Caleb opened his eyes he saw them struggling to pull the covers into reach with their tail. The appendage was not made for grasping, but eventually they did manage to get the blanket to their hand and cover the both of them. It would have been easier for them to sit up to do it, and Caleb couldn’t help but feel loved. They hadn’t wanted to disturb him.

“ _Ich liebe dich…”_ Caleb whispered after a while, hoping they wouldn’t hear.

“Hmm?”

 _Fick._ “Oh, I was just thanking you, Mollymauk. It is nothing.”

“Alright, Caleb. Get some sleep.” The fingers ran through his hair again.

“Okay,” he agreed, lulled to sleep by Molly’s gentle touch as he reflected on how deeply smitten he was. There would likely be consequences in the morning, but right now all Caleb could think about was how lucky he was.


End file.
